Journal
BIOCHEMICAL ENGINEERING JOURNAL
Volume 83, Issue -, Pages 97-103Publisher
ELSEVIER
DOI: 10.1016/j.bej.2013.12.009
Keywords
Biocatalysis; Chiral systems; Enantioseparation; (S)-3-Cyano-5-methyl hexanoic acid; High DMSO concentration tolerance; Optimization
Funding
- National High Technology Research and Development Program of China [2012AA022201]
- Key Scientific and Technology Programs of Zhejiang Province [2012C03005-2]
- National Major Project of Scientific Instruments Development of China [2012YQ150087]
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A novel biocatalytic route for (S)-3-cyano-5-methylhexanoic acid, the key chiral intermediate of pregabalin, was successfully developed using whole cells of newly isolated Arthrobacter sp. ZJB-09277. Kinetic resolution of a series of roc-3-cyano-5-methylhexanoic acid esters bearing a beta-stereocenter indicated that steric effect of the leaving alcohol moiety played an important role in determining activity and enantioselectivity of Arthrobacter sp. ZJB-09277 esterase. Enantiomeric ratio of the esterase toward rac-3-cyano-5-methylhexanoic acid ethyl ester was significantly increased from 33 to 80 by addition of 50% (v/v) DMSO and key reaction parameters optimization. The whole-cell catalysts exhibited strong tolerance against high DMSO concentration up to 80% (v/v). Enzymatic resolution of the substrate at a concentration of 100 mM gave (S)-3-cyano-5-methylhexanoic acid in 44.6 mM and 95.1% ee, which greatly increased the feasibility of this bioprocess to become an industrial approach. (C) 2013 Elsevier B.V. All rights reserved.
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